Summary of Vogel’s Textbook of Practical Organic Chemistry

New Edition

5th Edition

Authors of: Vogel’s Textbook of Practical Organic Chemistry

Brian S. Furniss

Antony J. Hannaford

Peter W. G. Smith

Austin R. Tatchell

Table of Contents in Vogel’s Textbook of Practical Organic Chemistry

CHAPTER 1 ORGANIC SYNTHESIS

1.1 INTRODUCTION

1.2 STRUCTURE OF THE TARGET MOLECULE

1.3 REACTION MECHANISM AND THE METHODOLOGY OF SYNTHESIS

1.4 REACTION MECHANISM AND THE STRATEGY OF SYNTHESIS

1.5 CONCLUSION

CHAPTER 2 EXPERIMENTAL TECHNIQUES

2.1 GENERAL INSTRUCTIONS FOR SAFE WORKING IN ORGANIC CHEMICAL LABORATORIES

2.2 PLANNING OF EXPERIMENTS AND RECORDING OF RESULTS

2.3 HAZARDS IN ORGANIC CHEMISTRY LABORATORIES

2.3.1 Introduction

2.3.2 Explosion and fire hazards

2.3.3 Reactive inorganic reagents

2.3.4 Hazards due to toxic chemicals

2.3.5 Electrical safety

2.3.6 Ultraviolet radiation

APPARATUS AND REACTION PROCEDURES

2.4 INTERCHANGEABLE GROUND GLASS JOINTS

2.5 TYPES OF GROUND GLASS JOINTS

2.6 CARE AND MAINTENANCE OF GROUND GLASS JOINTS

2.7 APPARATUS WITH INTERCHANGEABLE GROUND GLASS JOINTS

SUITABLE FOR GENERAL USE IN PREPARATIVE ORGANIC CHEMISTRY

2.8 OTHER TYPES OF INTERCHANGEABLE JOINTS AND STOPCOCKS

2.9 THE USE OF CORKS AND RUBBER STOPPERS

2.10 CUTTING AND BENDING OF GLASS TUBING

2.11 GENERAL LABORATORY APPARATUS

2.12 COOLING OF REACTION MIXTURES

2.13 HEATING OF REACTION MIXTURES

2.14 MECHANICAL AGITATION

2.15 TYPICAL GROUND GLASS JOINT ASSEMBLIES FOR STANDARD REACTION PROCEDURES

2.16 PRECAUTIONS FOR UNATTENDED REACTIONS

2.17 APPARATUS FOR SPECIAL REACTION TECHNIQUES

2.17.1 Catalytic hydrogenation

2.17.2 Reactions under pressure

2.17.3 Uncatalysed and catalysed vapour phase reactions

2.17.4 Ozonolysis

2.17.5 Organic photochemistry

2.17.6 Electrolytic (anodic) syntheses

2.17.7 Liquid ammonia techniques

2.17.8 Reactions involving air-sensitive compounds

ISOLATION AND PURIFICATION PROCESSES

2.18 GENERAL CONSIDERATIONS

2.19 FILTRATION TECHNIQUES

2.20 RECRYSTALLISATION TECHNIQUES

2.21 SUBLIMATION TECHNIQUES – FREEZE DRYING

2.22 SOLVENT EXTRACTION

2.23 DRYING OF LIQUIDS OR OF SOLUTIONS OF ORGANIC COMPOUNDS IN ORGANIC SOLVENTS

2.24 DISTILLATION AT ATMOSPHERIC PRESSURE

2.25 STEAM DISTILLATION

2.26 FRACTIONAL DISTILLATION AT ATMOSPHERIC PRESSURE

2.27 DISTILLATION UNDER DIMINISHED PRESSURE (“VACUUM’ DISTILLATION)

2.28 HIGH VACUUM DISTILLATION – MOLECULAR DISTILLATION

2.29 VACUUM PUMPS

2.30 MANOMETERS, VACUSTATS, VACUUM GAUGES AND MANOSTATS

2.31 CHROMATOGRAPHY

2.32 STORAGE OF SAMPLES

DETERMINATION OF PHYSICAL CONSTANTS

2.33 MELTING POINT – MIXED MELTING POINTS

2.34 DETERMINATION OF BOILING POINT

2.35 DETERMINATION OF MOLECULAR WEIGHT

2.36 DETERMINATION OF OPTICAL ROTATORY POWER

2.37 DETERMINATION OF REFRACTIVE INDEX

CHAPTER 3 SPECTROSCOPIC METHODS AND THE INTERPRETATION OF SPECTRA

Introduction

The electromagnetic spectrum

3.1 INFRARED SPECTROSCOPY

Instrumental features of infrared spectrophotometers

Determination of infrared spectra

Sample preparation

Features of an infrared spectrum

Interpretation of an infrared spectrum

Characteristic group frequencies

3.2 NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY

Features of the nuclear magnetic resonance spectrum

The chemical shift

Spin-spin splitting

Protons attached to heteroatoms

Simplification of 1H spectra

Interpretation of the p.m.r. spectrum

Further information from 13C-spectra

3.3 MASS SPECTROMETRY

The mass spectrum

Appearance of the mass spectrum

Interpretation of the mass spectrum

Mass spectra of classes of organic compounds

Instrumental features of ultraviolet-visible spectrophotometers

Determination of ultraviolet-visible spectra

Laws of light absorption

Solvents for ultraviolet spectroscopy

Solution preparation

Optical cells and their care

Features of an ultraviolet-visible spectrum

REFERENCES

CHAPTER 4 SOLVENTS AND REAGENTS

4.1 THE PURIFICATION OF COMMON ORGANIC SOLVENTS

Saturated aliphatic hydrocarbons

Aromatic hydrocarbons

Halogenated hydrocarbons

Aliphatic alcohols

Ethers

Ketones

Esters

Nitrogen-containing solvents

Sulphur-containing solvents

Phosphorus-containing solvents

4.2 THE PREPARATION AND PURIFICATION OF REAGENTS

REFERENCES

CHAPTER 5 ALIPHATIC COMPOUNDS

5.1 ALKANES

Structure

Summary of preparative methods and of retrosynthetic strategies

5.1.1 The catalytic hydrogenation and chemical reduction of alkenes

5.1.2 The hydrolysis of alkylmagnesium halides and the

hydrogenolysis of alkyl halides and of alkyl methane- or

toluene-/7-sulphonates

5.1.3 The reduction of aldehydes and ketones

5.1.4 Coupling reactions (a) using organometallic compounds, and

(b) at the anode

5.2 ALKENES Structure

Summary of preparative methods and of retrosynthetic strategies

Spectroscopic features

5.2.1 1,2-Elimination processes beta-elimination

5.2.2 The partial hydrogenation of alkynes

5.2.3 Wittig and related reactions

5.2.4 Selected rearrangements of alkynes to allenes

5.3 ALKYNES Structure

CHAPTER 6 AROMATIC COMPOUNDS

CHAPTER 7 SELECTED ALICYCLIC COMPOUNDS

CHAPTER 8 SELECTED HETEROCYCLIC COMPOUNDS

CHAPTER 9 INVESTIGATION AND CHARACTERISATION OF ORGANIC COMPOUNDS

CHAPTER 10 PHYSICAL CONSTANTS OF ORGANIC COMPOUNDS

Index to tables

APPENDICES

Index

Reference data

Abbreviations

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